115551-46-7

Usage

Uses

Used in Pharmaceutical Industry:
3-N-CBZ-AMINOPYRROLIDINE is used as a key intermediate for the synthesis of various pharmaceuticals due to its ability to facilitate the creation of complex molecular structures. Its role in the production of heterocyclic compounds, which are prevalent in many drug molecules, makes it an essential component in drug discovery and development processes.
Used in Agrochemical Industry:
In the agrochemical sector, 3-N-CBZ-AMINOPYRROLIDINE is utilized as a reagent in the synthesis of agrochemicals, contributing to the development of pesticides, herbicides, and other crop protection agents. Its versatility in organic synthesis allows for the creation of novel compounds with improved efficacy and selectivity.
Used in Organic Synthesis Research:
3-N-CBZ-AMINOPYRROLIDINE is employed as a research tool in organic chemistry, where it is used to explore new synthetic pathways and develop innovative methodologies. Its unique reactivity and the presence of the carbobenzoxy group make it an attractive candidate for studying reaction mechanisms and developing new synthetic strategies.
Used as an Enzyme Inhibitor:
3-N-CBZ-AMINOPYRROLIDINE has shown potential as an inhibitor of certain enzymes, making it a candidate for use in medicinal chemistry. Its ability to modulate enzyme activity could lead to the development of new therapeutic agents for various diseases and conditions.
Used in Drug Delivery Systems:
In the field of drug delivery, 3-N-CBZ-AMINOPYRROLIDINE may be utilized to improve the bioavailability and targeting of pharmaceutical agents. Its chemical properties can be leveraged to design drug delivery systems that enhance the efficacy and safety of medications.

InChI:InChI=1/C12H16N2O2/c15-12(14-11-6-7-13-8-11)16-9-10-4-2-1-3-5-10/h1-5,11,13H,6-9H2,(H,14,15)

Upstream product

• 79286-79-6 pyrrolidin-3-amine 
• 501-53-1 benzyl chloroformate 
• 325775-36-8 tert-butyl 3-{[(benzyloxy)carbonyl]amino}-1-pyrrolidinecarboxylate 

Downstream Products

• 115551-00-3 10-[3-(benzyloxycarbonylamino)-1-pyrrolidinyl]-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[3,2,1-ij]-1,3,4-benzoxadiazine-6-carboxylic acid 
• 1083175-60-3 tert-butyl (2S)-5-(3-{[(benzyloxy)carbonyl]amino}pyrrolidin-1-yl)-2-{bis[(tert-butoxy)carbonyl]amino}pentanoate 

Relevant academic research and scientific papers

Design, synthesis and SAR of antitubercular benzylpiperazine ureas

Abstract: N-furfuryl piperazine ureas disclosed by scientists at GSK Tres Cantos were chosen as antimycobacterial hits from a phenotypic whole-cell screen. Bioisosteric replacement of the furan ring in the GSK Tres Cantos molecules with a phenyl ring led to molecule (I) with an MIC of 1?μM against Mtb H37Rv, low cellular toxicity (HepG2 IC50 ~ 80?μM), good DMPK properties and specificity for Mtb. With the aim of delineating the SAR associated with (I), fifty-five analogs were synthesized and screened against Mtb. The SAR suggests that the piperazine ring, benzyl urea and piperonyl moieties are essential signatures of this series. Active compounds in this series are metabolically stable, have low cellular toxicity and are valuable leads for optimization. Molecular docking suggests these molecules occupy the Q0 site of QcrB like Q203. Graphic Abstract: Bioisosteric replacement of N-furfuryl piperazine-1-carboxamides yielded molecule (I) a novel lead with satisfactory PD, metabolism, and toxicity profiles.[Figure not available: see fulltext.]

Discovery of 2-substituted 1H-benzo[d]immidazole-4-carboxamide derivatives as novel poly(ADP-ribose)polymerase-1 inhibitors with in?vivo anti-tumor activity

Novel 1H-benzo[d]immidazole-4-carboxamide derivatives bearing five-membered or six-membered N-heterocyclic moieties at the 2-position were designed and synthesized as PARP-1 inhibitors. Structure-activity relationships were conducted and led to a number of potent PARP-1 inhibitors having IC50 values in the single or double digit nanomolar level. Some potent PARP-1 inhibitors also had similar inhibitory activities against PARP-2. Among all the synthesized compounds, compound 10a and 11e displayed strong potentiation effects on temozolomide (TMZ) in MX-1?cells (PF50?=?7.10, PF50?=?4.17). In?vivo tumor growth inhibition was investigated using compound 10a in combination with TMZ, and it was demonstrated that compound 10a could strongly potentiate the cytotoxicity of TMZ in MX-1 xenograft tumor model. Two co-crystal structures of compounds 11b and 15e complexed with PARP-1 were achieved and demonstrated a unique binding mode of these benzo-imidazole derivatives.

PROCESS FOR PRODUCING NITROGENOUS HETEROCYCLIC COMPOUND

A nitrogenous heterocyclic compound such as 3-aminopyrrolidine derivative is produced by hydrogenolysis of an N-substituted nitrogenous heterocyclic compound with normal pressure hydrogen in a water-based solvent in presence of a catalyst. In the case an optically active 1-substituted-3-aminopyrrrolidine derivative is used as a raw material, an optically active 3-aminopyrrolidine derivative can be obtained as a product practically without racemination.

Novel, nonpeptidic cyanamides as potent and reversible inhibitors of human cathepsins K and L

Compounds containing a 1-cyanopyrrolidinyl ring were identified as potent and reversible inhibitors of cathepsins K and L. The original lead compound 1 inhibits cathepsins K and L with IC50 values of 0.37 and 0.45 μM, respectively. Modification of compound 1 by replacement of the quinoline moiety led to the synthesis of N-(1-cyano-3-pyrrolidinyl)benzenesulfonamide (2). Compound 2 was found to be a potent inhibitor of cathepsins K and L with a Ki value of 50 nM for cathepsin K. Replacement of the 1-cyanopyrrolidine of compound 2 by a 1-cyanoazetidine increased the potency of the inhibitor by 10-fold. This increase in potency is probably due to an enhanced chemical reactivity of the compound toward the thiolate of the active site of the enzyme. This is demonstrated when the assay is performed in the presence of glutathione at pH 7.0 which favors the formation of a GSH thiolate anion. Under these assay conditions, there is a loss of potency in the 1-cyanoazetidine series due to the formation of an inactive complex between the GSH thiolate and the 1-cyanoazetidine inhibitors. 1-Cyanopyrrolidinyl inhibitors exhibited time-dependent inhibition which allowed us to determine the association and dissociation rate constants with human cathepsin K. The kinetic data obtained showed that the increase of potency observed between different 1-cyanopyrrolidinyl inhibitors is due to an increase of kon values and that the association of the compound with the enzyme fits an apparent one-step mechanism. 13C NMR experiments performed with the enzyme papain showed that compound 2 forms a covalent isothiourea ester adduct with the enzyme. As predicted by the kinetic analysis, the addition of the irreversible inhibitor E64 to the enzyme-cyanopyrrolidinyl complex totally abolished the signal of the isothiourea bond as observed by 13C NMR, thereby demonstrating that the formation of the covalent bond with the active site cysteine residue is reversible. Finally, compound 2 inhibits bone resorption in an in vitro assay involving rabbit osteoclasts and bovine bone with an IC50 value of 0.7 μM. 1-Cyanopyrrolidine represents a new class of nonpeptidic compounds that inhibit cathepsin K and L activity and proteolysis of bone collagen.